29040-52-6

Basic information

• Product Name: Benzofuran, 6-methoxy-3-methyl-
• Synonyms: Benzofuran, 6-methoxy-3-methyl-;6-Methoxy-3-Methylbenzofuran
• CAS NO: 29040-52-6
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• Mol File: 29040-52-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: Benzofuran, 6-methoxy-3-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzofuran, 6-methoxy-3-methyl-(29040-52-6)
• EPA Substance Registry System: Benzofuran, 6-methoxy-3-methyl-(29040-52-6)

Safety Data

• Hazardous Substances Data: 29040-52-6(Hazardous Substances Data)

Usage

General Description

Benzofuran, 6-methoxy-3-methyl-, also known as 6-MeO-3-MeO-BF, is a chemical compound with a molecular formula C10H10O2. It is a derivative of benzofuran, a heterocyclic compound with a furan ring fused to a benzene ring. 6-MeO-3-MeO-BF is a light yellow liquid that is used in various drug and pharmaceutical applications, including as a potential psychoactive substance. It has also been identified as a potential impurity in illicit drugs. The compound is of interest to researchers and regulatory authorities due to its potential effects on human health and its presence in illegal drug formulations.

Upstream product

• 6437-63-4 1-(3-methoxyphenoxy)propan-2-one 
• 13246-19-0 (2-acetyl-5-methoxy-phenoxy)-acetic acid ethyl ester 
• 7664-93-9 sulfuric acid 
• 898826-74-9 3-allyloxy-4-chloroanisole 
• 150-19-6 O-methylresorcine 
• 2555-28-4 4-methyl-7-methoxy-2H-1-benzopyran-2-one 

Downstream Products

• 10410-30-7 β-<6-Methoxy-3-methyl-2-benzofuryl>-propionsaeure 
• 10410-28-3 6-methoxy-3-methylbenzofuran-2-carbaldehyde 
• 53724-96-2 ethyl 6-methoxy-3-methylbenzofuran-2-carboxylate 
• 10410-29-4 6-methoxy-3-methyl-benzofuran-2-carboxylic acid 

Relevant articles and documents

Discovery of 4,6-bis(benzyloxy)-3-phenylbenzofuran as a novel Pin1 inhibitor to suppress hepatocellular carcinoma via upregulating microRNA biogenesis

Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (Pin1)participates in diverse cancer-associated signaling pathways, playing an oncogenic role in multiple human cancers, including hepatocellular carcinoma (HCC). Our recent works clarify that Pin1 modulates miRNAs biogenesis by interacting with ERK-phosphorylated exportin-5 (XPO5)and changing XPO5 conformation, giving a potential target for HCC treatment. Herein, we discover 4,6-bis(benzyloxy)-3-phenylbenzofuran (TAB29)as a novel Pin1 inhibitor that targets Pin1 PPIase domain. TAB29 potently inhibits Pin1 activity with the IC50 value of 874 nM and displays an excellent selectivity toward Pin1 in vitro. Cell-based biological evaluation reveals that TAB29 significantly suppresses cell proliferation of HCC cells through restoring the nucleus-to-cytoplasm export of XPO5 and upregulating mature miRNAs expression. Collectively, this work provides a promising small molecule lead compound for Pin1 inhibition, highlighting the therapeutic potential of miRNA-based treatment for human cancers.

Intramolecular photoarylation of alkenes by phenyl cations

Acetone-sensitized irradiation of various o-chlorophenyl allyl ethers in polar solvents led to either (dihydro)benzofurans or chromanes. The reaction appeared to involve photoheterolysis of the aryl-Cl bond followed by phenyl cation addition onto the tethered double bond either in 5-exo or 6-endo modes. The adduct cation gave the end products by deprotonation: addition of chloride anion or of the solvent, depending on the struc ture: and the conditions used. Preference for the 5-exo mode increased in passing from medium polarity (methylene chloride, ethyl acetate) to high polarity solvents (aqueous acetonitrile, methanol, 2,2,2-trifluoroethanol), for which this was often the exclusive path. The same compounds underwent photohomolysis when irradiated in cyclohexane, and radical cyclization was one of the process occurring. Substitution of a methylene group for the ether oxygen atom made 6-endo cyclization by far the main path in a related o-chlorophenylbutene. Again, the selectivity was higher in polar protic solvents. The results are discussed in terms of in cage ion pair versus free phenyl cation reactions.

Benzofuran Derivatives. Part 4. Synthesis of Benzofurans and 2,3,4,5-Tetrahydro-1-benzoxepin-3,5-diones

By treatment of ethyl 4- or 5-substituted 2-acetylphenoxyacetates 1 with potassium hydroxide in dry dioxane, benzofurans 2-7 and 2,3,4,5-tetrahydro-1-benzoxepin-3,5-diones 8 were obtained.The relative yields of benzofurans 2-7 and 2,3,4,5-tetrahydro-1-benzoxepin-3,5-diones 8 varied with the types of 4- or 5-substituents.The electron-donating 4-methoxyl group favored the formation of benzoxepins.On the other hand, electron-withdrawing substituents such as the 4-nitro group favored the formation of benzofurans.When esters 1 were treated with sodium amide,2,3-dihydrobenzofurans 2 were obtained exclusively regardless of 4- or 5-substituents.